3-Butanoyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-carboxylic Acid

ID: ALA1800991

Chembl Id: CHEMBL1800991

PubChem CID: 49851171

Max Phase: Preclinical

Molecular Formula: C30H37NO5

Molecular Weight: 491.63

Molecule Type: Small molecule

Names and Identifiers

Canonical SMILES:  CCCCCCCCc1ccc(OCC(=O)Cn2cc(C(=O)CCC)c3cc(C(=O)O)ccc32)cc1

Standard InChI:  InChI=1S/C30H37NO5/c1-3-5-6-7-8-9-11-22-12-15-25(16-13-22)36-21-24(32)19-31-20-27(29(33)10-4-2)26-18-23(30(34)35)14-17-28(26)31/h12-18,20H,3-11,19,21H2,1-2H3,(H,34,35)

Standard InChI Key:  LYTDGMCHCCNIHS-UHFFFAOYSA-N

Alternative Forms

1. Parent:

   

   ALA1800991

   3-Butanoyl-1-[3-(4-octylphenoxy)-2-oxopropyl]indole-5-carboxylic acid

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 491.63

Molecular Weight (Monoisotopic): 491.2672

AlogP: 6.87

#Rotatable Bonds: 16

Polar Surface Area: 85.60

Molecular Species: ACID

HBA: 5

HBD: 1

#RO5 Violations: 1

HBA (Lipinski): 6

HBD (Lipinski): 1

#RO5 Violations (Lipinski): 1

CX Acidic pKa: 3.63

CX Basic pKa: ┄

CX LogP: 7.61

CX LogD: 4.27

Aromatic Rings: 3

Heavy Atoms: 36

QED Weighted: 0.17

Np Likeness Score: -0.36

References

1. Bovens S, Schulze Elfringhoff A, Kaptur M, Reinhardt D, Schäfers M, Lehr M..  (2010)  1-(5-Carboxyindol-1-yl)propan-2-one inhibitors of human cytosolic phospholipase A2α: effect of substituents in position 3 of the indole scaffold on inhibitory potency, metabolic stability, solubility, and bioavailability.,  53  (23): [PMID:21067218] [10.1021/jm101094p]

2. Arnsmann M, Hanekamp W, Elfringhoff AS, Lehr M..  (2017)  Structure-activity relationship studies on 1-(2-oxopropyl)indole-5-carboxylic acids acting as inhibitors of cytosolic phospholipase A2α: Effect of substituents at the indole 3-position on activity, solubility, and metabolic stability.,  125  [PMID:27810597] [10.1016/j.ejmech.2016.10.039]

Source

Source(1):

• Scientific Literature